Before we start getting into all of the many confusing aspects of Rory Gilmore's love life, we will say that we love Rory to bits. The entire Gilmore Girl series is a real masterpiece and that's largely due to how amazing Lorelai and Rory were both written and played. That being said, the more we rewatch this show, the harder it becomes to ignore all of the issues surrounding Rory and her many relationships. While Lorelai has her fair share of confusing romantic moments as well, like ignoring her feelings for Luke for over a decade, Rory has still got her beat.
Today, we will be looking back at all of Rory's relationships over the years and revealing the most confusing aspects about them. It really doesn't matter if we're team Jess, Dean or Logan, because in the end, none of their time with Rory made all that much sense.
15 Her Kiss-And-Run With Jess Was Mean To Everyone Involved
Let's head back to Sookie's wedding day for a moment. Putting Lorelai's issues that episode aside, we saw Rory plant a kiss on Jess (while she was still dating Dean, of course), tell him immediately not to say anything, then bolted and disappeared for the whole summer without a word. What did this accomplish other than hurt absolutely everyone?
14 Dead And Rory's 'I Love You' Breakup Didn't Make Sense And Went On For Way Too Long
This was an insanely frustrating storyline to get through. All it would have taken was a quick 2 minute convo to clear things up and everything would have been fine. It's not confusing that Rory wanted to wait before saying it back, but the breakup was dramatic and sent the whole town after Dean. All of that and then Rory just decided to say it. UGH!
13 Logan Shouldn't Have Been Blamed For Sleeping With Honor's Friends While He And Rory Were On A Break
If Rory had only been mad about how Honor's friends had treated her that day, we would have totally understood. They were the worst. However, to get mad enough at Logan to end things because he had been with a few of them during their break, wasn't right. Logan truly thought they were broken up. Who does she think she is, Rachel Green?
12 Rory's Quick To Accuse Logan Of Cheating, But She Clearly Doesn't Have A Problem Being The Other Woman
This is one of Rory's more confusing traits. She stayed mad for a long time about Logan hooking up with those girls during their break, but she's also proven time and time again that she doesn't really care about monogamy. She was fine being Dean's other woman and then was fine being Logan's during the revival! Not cool!
11 She Loved Jess From The Moment They Met, So Why Stay With Dean For So Long?
It was obvious that Jess and Rory were feeling each other pretty much the second he arrived in Stars Hollow. She would pretend she hated him, but constantly find ways to spend time with him. If she really didn't care for him, why go on that basket lunch? But she refused to break things off with Dean, even when she saw what it was doing to him.
10 Even After Choosing Jess, Rory Still Kept Dean Around!
For a smart girl, Rory really makes poor life choices. After the miserable public breakup that went down at the dance marathon, Rory was finally free to be happy with Jess and they were happy...for like a minute. However, Rory's need to keep Dean around as a friend was obviously going to ruin this. The winter carnival was so hard to watch.
9 Why Did She Think Going To Hang At Dean's Parent's House Would Be A Fun Date After She Ruined His Marriage?
The way Rory and Dean just assumed they could kick their romance off from where they had left it as teenagers was so weird. Dean was married and the way his wife found out about Rory was brutal. It's common sense that his parents wouldn't be huge fans of Rory's anymore, though it didn't seem to occurred to either of them.
8 Not That He Cared, But Rory Totally Used Robert
Rory is really painted out to be sweet and innocent with an excellent head on her shoulders, but the girl does have a conniving side. After Logan told her he didn't want a relationship, she showed up to a party with one of his best friends, obviously knowing it would be enough to get him to commit. Unfortunately for Robert, it totally worked.
7 She Really Didn't Understand Why Her Mom Was Mad When She Caught Her With Dean (Who Was Married)
It was never fun to watch these two fight. While Lorelai can be blamed for some of their tiffs, she was very much in the right during this specific one. Rory lost her v-card to Dean (while he was married) and got busted by her mom. When Lorelai rightfully expressed her disappointment, Rory snapped and accused her of ruining her special night!
6 Rory's Romances Eventually Eclipsed Everything She Had Been About At The Beginning
Originally, Rory's entire character revolved around her being a bright kid with the potential to do anything she wanted. However, as the show progressed, Rory seemed to push all of her goals and dreams aside to deal with her never-ending relationship dramas. Jess finally calling her out on this was one of the best scenes of the season.
5 Leading Jess On In Philly Was So Wrong
As happy as we were to get the chance to catch up with Jess and see that he was doing great in Philadelphia, the reunion was marred by Rory leading him to believe he might finally have a chance at winning her back. She wanted sympathy for what Logan had supposedly done to her, but that wasn't Jess' problem.
4 Marty Deserved Better
Now, we are not blaming Rory for not returning Marty's feelings. You either feel a spark or you don't. But, Rory should have kindly ended their friendship and explained to him that she didn't want to lead him on. She definitely should NOT have had him tag along on a group date with Logan.
3 Jess Is Obviously The Right Choice, But He's The One She Dated For The Least Amount Of Time
Rory loves making pro/con lists, it's her thing. If she had made one about her relationship options, it would have definitely come out in Jess' favor, especially in the later seasons. She and Jess always had the most in common, the best chemistry and let's get real, Milo Ventimiglia is gorgeous. However, Rory dated both Logan and Dean for way longer than Jess.
2 The Emily-Rory-Jess Dinner Was As Cringy As Things Get
This was a tough episode to get through. Jess agreed to meet Rory's grandmother, which we all know is a very daunting thing considering who Emily Gilmore is. However, when he showed up with a black eye, she attacked him right in front of Emily! Major props to grandma Gilmore though, she handled it like a champ.
1 Does Anyone Even Remember The Name Of Her Boyfriend In The Revival?
Ok, we know his name is Paul, but you get our point. The whole joke surrounding this guy was that Rory kept forgetting she had a boyfriend. That's pretty brutal and even worse when we think about the fact that she was sleeping with Logan the entire time. Get it together, girl!
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